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Relative Binding Affinities of Alkali Metal Cations to [18]Starand in Methanol: Computational and Experimental Studies

Hwang, Sungu and Lee, Kwan Hee and Ryu, Gean Ha and Jang, Yun Hee and Lee, Sang Bok and Lee, Woo Young and Hong, Jong-In and Chung, Doo Soo (2000) Relative Binding Affinities of Alkali Metal Cations to [18]Starand in Methanol: Computational and Experimental Studies. Journal of Organic Chemistry, 65 (2). pp. 536-542. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20170427-093910923

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Abstract

The binding affinity and selectivity of a new ionophore, [1_8]starand (1), toward alkali metal cations in methanol were examined through NMR titration experiments and free energy perturbation (FEP) and molecular dynamics simulations. The preference was determined to be K^+ > Rb^+ > Cs^+ > Na^+ ≫ Li^+ in both FEP simulations and NMR experiments. The FEP simulation results were able to predict the relative binding free energies with errors less than 0.13 kcal/mol, except for the case between Li^+ and Na^+. The cation selectivity was rationalized by analyzing the radial distribution functions of the M−O and M−C distances of free metal cations in methanol and those of metal−ionophore complexes in methanol.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jo991480jDOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo991480jPublisherArticle
ORCID:
AuthorORCID
Chung, Doo Soo0000-0002-8335-3201
Additional Information:© 2000 American Chemical Society. Received 20 September 1999. Published online 30 December 1999. Published in print 1 January 2000. This work was supported by the Korea Science and Engineering Foundation (KOSEF 96-0501-08-01-3), and the Basic Science Research Institute Program (BSRI-97-3416, 3418). S.H. acknowledges a postdoctoral research fellowship from the Korea Research Foundation.
Funders:
Funding AgencyGrant Number
Korea Science and Engineering FoundationKOSEF 96-0501-08-01-3
Basic Science Research InstituteBSRI-97-3416, 3418
Korea Research FoundationUNSPECIFIED
Record Number:CaltechAUTHORS:20170427-093910923
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20170427-093910923
Official Citation:Relative Binding Affinities of Alkali Metal Cations to [18]Starand in Methanol:  Computational and Experimental Studies Sungu Hwang, Kwan Hee Lee, Gean Ha Ryu, Yun Hee Jang, Sang Bok Lee, Woo Young Lee, Jong-In Hong, and Doo Soo Chung The Journal of Organic Chemistry 2000 65 (2), 536-542 DOI: 10.1021/jo991480j
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76990
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:27 Apr 2017 22:21
Last Modified:22 May 2017 16:47

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